NP-MRD: Showing NP-Card for 1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate (NP0160328)

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Record Information

Version

2.0

Created at

2022-09-02 18:15:28 UTC

Updated at

2022-09-02 18:15:28 UTC

NP-MRD ID

NP0160328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate

Description

14-Acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl 3,4-dimethylpent-2-enoate belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. 1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate is found in Cynanchum auriculatum and Cynanchum caudatum. 14-Acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl 3,4-dimethylpent-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522252D          

 65 71  0  0  0  0            999 V2000
   -5.1355    4.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6037    4.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916    4.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598    3.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4477    3.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9158    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    2.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083    2.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    2.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    1.5765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446    1.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    1.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8522    2.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5719    2.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0370    0.1699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5052   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4128    0.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -0.9463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7855   -1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976   -1.3819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1295   -0.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4599    1.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0235    0.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7280   -0.6856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5996   -1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315   -1.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799   -0.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1674    4.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    5.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189    6.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5113    5.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431    5.7964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 38 36  1  4  0  0  0
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 39 40  1  0  0  0  0
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 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
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 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 44 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 32 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 30 56  1  0  0  0  0
 56 57  1  0  0  0  0
 27 57  1  0  0  0  0
 46 58  1  0  0  0  0
 58 59  2  0  0  0  0
 58 60  1  0  0  0  0
  5 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
  3 64  1  0  0  0  0
 64 65  1  0  0  0  0
M  END

     RDKit          3D

143149  0  0  0  0  0  0  0  0999 V2000
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    2.8774    0.1261    1.0941 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8682   -0.2903    2.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9154    1.2251    0.4633 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8890    2.1370    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161522252D          

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M  END
> <DATABASE_ID>
NP0160328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2C(C)OC(CC2OC)OC2C(C)OC(CC2OC)OC2CCC3(C)C4CC(OC(=O)C=C(C)C(C)C)C5(C)C(O)(CCC5(O)C4(O)CC=C3C2)C(C)=O)OC(C)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C49H78O16/c1-25(2)26(3)19-38(51)63-37-24-36-45(8)15-14-32(20-31(45)13-16-48(36,54)49(55)18-17-47(53,30(7)50)46(37,49)9)62-39-22-34(57-11)43(28(5)60-39)65-41-23-35(58-12)44(29(6)61-41)64-40-21-33(56-10)42(52)27(4)59-40/h13,19,25,27-29,32-37,39-44,52-55H,14-18,20-24H2,1-12H3

> <INCHI_KEY>
YLHXSKZGPASTOD-UHFFFAOYSA-N

> <FORMULA>
C49H78O16

> <MOLECULAR_WEIGHT>
923.147

> <EXACT_MASS>
922.528986432

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
143

> <JCHEM_AVERAGE_POLARIZABILITY>
102.05846412043607

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoate

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
4.7702363640000005

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.941186494559716

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.33171586260108

> <JCHEM_PKA_STRONGEST_BASIC>
-3.508022603433697

> <JCHEM_POLAR_SURFACE_AREA>
207.35999999999999

> <JCHEM_REFRACTIVITY>
234.73200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -9.586   9.101   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.594   7.923   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.078   8.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.085   7.017   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.569   7.288   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.576   6.111   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.099   4.662   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.615   4.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.608   5.569   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.139   2.943   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.146   1.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.630   2.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.107   3.485   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.591   3.756   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.068   5.204   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.669   0.317   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.676  -0.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.160  -0.589   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.637   0.859   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.168  -1.766   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.691  -3.215   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.207  -3.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.200  -2.309   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.716  -2.580   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.708  -1.402   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.928  -0.140   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.935   1.037   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.458   2.486   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.419   0.766   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.427   1.944   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.950   3.392   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.911   1.672   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.918   2.850   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.387   0.224   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.826  -1.280   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.939  -5.912   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.453  -2.545   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      11.445  -3.722   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      10.976  -1.096   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -4.046   8.736   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -5.038   9.914   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -4.515  11.362   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -6.554   9.643   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -7.547  10.820   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   64                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   61                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   57                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   56                                             
CONECT   31   30                                                            
CONECT   32   30   33   52                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   44                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   34   45   46   50                                             
CONECT   45   44                                                            
CONECT   46   44   47   48   58                                             
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   44   51   52                                             
CONECT   51   50                                                            
CONECT   52   50   32   53   54                                             
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   30   57                                                  
CONECT   57   56   27                                                       
CONECT   58   46   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61    5   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62    3   65                                                  
CONECT   65   64                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  142    0
END

View in JSmol

Synonyms

Value	Source
14-Acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoic acid	Generator
14-Acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoic acid	Generator

Chemical Formula

C₄₉H₇₈O₁₆

Average Mass

923.1470 Da

Monoisotopic Mass

922.52899 Da

IUPAC Name

14-acetyl-10,11,14-trihydroxy-5-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1CC(OC2C(C)OC(CC2OC)OC2C(C)OC(CC2OC)OC2CCC3(C)C4CC(OC(=O)C=C(C)C(C)C)C5(C)C(O)(CCC5(O)C4(O)CC=C3C2)C(C)=O)OC(C)C1O

InChI Identifier

InChI=1S/C49H78O16/c1-25(2)26(3)19-38(51)63-37-24-36-45(8)15-14-32(20-31(45)13-16-48(36,54)49(55)18-17-47(53,30(7)50)46(37,49)9)62-39-22-34(57-11)43(28(5)60-39)65-41-23-35(58-12)44(29(6)61-41)64-40-21-33(56-10)42(52)27(4)59-40/h13,19,25,27-29,32-37,39-44,52-55H,14-18,20-24H2,1-12H3

InChI Key

YLHXSKZGPASTOD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cynanchum auriculatum	LOTUS Database	35616633
Cynanchum caudatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Organoheterocyclic compound
Ether
Secondary aliphatic amine
Azacycle
Secondary amine
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.86	ALOGPS
logP	4.77	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	207.36 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	234.73 m³·mol⁻¹	ChemAxon
Polarizability	102.06 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate (NP0160328)

MOL for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

3D MOL for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

3D SDF for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

3D-SDF for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

PDB for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

3D PDB for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

SMILES for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

INCHI for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

Structure for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)

3D Structure for NP0160328 (1-acetyl-1,3a,3b-trihydroxy-7-{[5-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-4-methoxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3,4-dimethylpent-2-enoate)